


Prompt | Afterschool Special

by wincesthart



Category: Supernatural
Genre: Bottom Dean, M/M
Language: English
Status: Completed
Published: 2016-07-24
Updated: 2016-07-24
Packaged: 2018-07-26 10:03:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 2,085
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7569922
Author URL: https://archiveofourown.org/users/wincesthart/pseuds/wincesthart
Summary: <blockquote class="userstuff">
              <p>Sam and Dean and that dang gym teacher outfit.</p>
            </blockquote>





	1. Prompt | Afterschool Special

**Summary for the Chapter:**

> cu11enrutherford-deactivated201 said: Can I have some wincesty smut. During afterschool special when dean and Sam are undercover at Truman high? Particularly Sam taking dean to the sports equipment closet near the gym and having intense sex with dean only wearing his red striped socks and sneakers--

It wasn’t hard to convince Dean to have sex in the sports equipment closet, as disturbing as that may sound, but he shoved him into the closet and pressed Dean to the back wall, pushing things out of the way to step up close behind his brother. Sam felt a shiver run through Dean as Sam trailed his fingers over Dean’s spine.

“Take off your shirt,” Sam whispered and Dean pulled away from the wall the tear his shirt off, throwing it on the ground in front of him and Sam hummed as he smoothed his hands over Dean’s shoulder blades, down his back and grabbing his waist, making Dean gasp softly.

“Now your shorts,” Sam said, grabbing the waistband of Dean’s shorts and snapping them against his back. Dean pulled them down, along with his underwear and stepped out of them, leaving him in his long socks, sneakers and his little red sweatband. Sam leaned in to kiss the shell of Dean’s ear, pressing up close to Dean’s back so Dean could feel his erection through his pants and Dean whined, pushing his hips back.

Sam smiled and bit Dean’s earlobe, reaching back to unzip his pants, right against Dean’s skin so Dean could feel Sam’s hand dragging his zipper down. Sam pulled out his cock and nudged it against Dean’s hole and Dean sighed, putting his hands on the wall and pushing back.

Sam just slid his hard dick between Dean’s ass cheeks and he pressed himself fully to Dean’s body, wrapping an arm around Dean’s waist, holding Dean close while his free hand wrapped around Dean’s dick, squeezing him and stroking him hard. Dean moaned, pushing forward into Sam’s hand and Sam bit Dean’s ear again.

“Feel good?” Sam asked quietly and Dean nodded eagerly and Sam squeezed harder. “Say it,” Sam whispered and Dean moaned.

“Yes, yes, fuck… Feels so fuckin’ good, Sam,” Dean panted. Sam humped up against Dean’s ass, stroking Dean hard and fast.

“Such a naughty little teacher,” Sam said, shoving his hips into Deans, “letting the janitor fuck you in a close during school hours?” Sam laughed and Dean could only whine. Sam pulled his hand away from Dean’s dick and Dean growled out Sam’s name, pushing his hips back but Sam ignored him, sticking his fingers in his mouth and sucking on them, licking the taste of Dean down and getting them wet.

Then he pressed his fingers to Dean’s hole, sliding them in and opening Dean up and Dean gasped when Sam began scissoring them, splitting him open. And they both knew Dean wasn’t fully ready but they needed it bad, so Sam slicked up his dick with his own spit, getting it as wet as he could and shoved into Dean hard, fucking him good and Sam had to hold onto Dean to keep his brother from falling over, his knees nearly giving in. 

“Gonna go out there and walk down the halls like you didn’t just get fucked up the ass, like my come isn’t leaking from you.” Sam muttered in Dean’s ear and Dean whimpered. He kept muttering fuckfuckfuck on every thrust, but Sam grabbed Dean’s jaw, held him still so Sam could shove into him, hitting his prostate just right and making Dean’s eyes roll back.

“But I’ll know,” Sam continued, “I’ll know how sexy you looked in only your little gym socks and sneakers. I know how nice your ass looked stretched around my dick. Oh, fuck, Dean…”

Dean cried out, getting close and Sam held onto Dean’s jaw with one hand but let his other hand slide down Dean’s torso to his cock, wrapping it up in his hand and stroking.

“Wanna fuck you in this again,” Sam said, “Want you on the bed with your ass in the air. And your little socks on, fuck.” Sam came inside Dean, picturing what he was saying and then Dean was pulsing around Sam, pulling him in deep and Sam groaned, grinding his hips a few more times against Dean’s ass.

Dean’s sweatband was soaking but he leaned forward, pressed his arm to the wall in front of him and rested his forehead ont his forearm. Sam kissed Dean’s bare shoulders as Dean reached down for Sam’s hand around his now soft dick, pulling him off and tangling their fingers together.

“Let’s go,” Dean whispered and Sam nodded, giving his brother’s ass a softly slap before pulling out.


	2. Prompt | Little Red Shorts

**Summary for the Chapter:**

> whiskeykissedsammy said to wincesthart:  
> Hello, hello. Will you please consider writing this continuation prompt with Wincest & Bottom!Dean. Sam discovers that Dean kept those gym shorts from that hunt at the high school, even though it's been like 7/8 years. Sam gets hard from the memories of their time in the janitor closet and starts jerking off. Dean catches him. The rest is up to you. ;) Please and thank you, friend!!

This is the fourth time this month Dean has stolen Sam’s favorite shirt and Sam’s getting really sick of it. He digs through his brother’s dresser, hair still wet from the shower and only wearing his jeans, since he still hasn’t found his shirt. He’s going through the last drawer when he pulls at something bright red. Sam knows Dean’s whole wardrobe and he does not recall Dean ever wearing something this red, or this bright. He pulls it out completely, buried and tangled with Dean’s other clothes, and realizes it’s a tiny pair of red gym shorts. It takes him a second to even remember where these might have come from, but he suddenly remembers; the hunt at their old school, Dean posing as the gym teacher, them fooling around in the supply closet.

“Fuck,” Sam breathes, looking down at the little shorts in his hand. He absently rubs the fabric together. Dean’s kept these all this time? Why would he keep these?

Sam’s mind starts to wander, thinks about when Dean wore them, how great his ass looked with that red fabric stretched over it. He remembers their time in the supply closet, the pretty noises Dean made…

Sam finds himself flat on his brother’s bed, sinking into the memory foam as he thinks about how good Dean would look in these shorts now. Dean’s body is a bit bigger now; his legs are stronger, hips a little wider, belly a little softer. Sam can imagine how nicely he’d fill these shorts out now. His hand finds the zipper on his jeans and he shoves his pants and underwear down just enough to get his dick out, already getting harder as he pictures his brother in the shorts.

He strokes himself lazily, rubs the fabric together in his other hand, closes his eyes and pictures his brother, ass in the air and little red shorts tight around him.

“What are you doing?” Sam hears from the doorway. He stops, looks up and sees his big brother standing there, hair rumpled like he just took a nap and watching interestedly.

“I-” Sam starts, and takes his hand off his dick, suddenly realizing what he’s doing, “I found something.” He leans up on one elbow and holds the shorts up in one hand towards Dean in explanation. Dean looks skeptical and walks forward, taking the tiny piece of fabric from Sam’s hand and examining it. “Why’d you keep them?” Sam asks as Dean keeps staring at the shorts.

“Well, ‘cause, you know, you said,” Dean starts, shrugs nonchalantly, suddenly embarrassed, “you said you wanted me to.”

Sam stares back dazedly. “I did?”

“Yeah!” Dean says, “said you wanted to fuck me in that outfit again, or something. So I did.” A wave of arousal goes through Sam as he suddenly remembers.

“Shit,” he groans, reaching for his dick again and squeezing at the base.

“So…” Dean says, eyes trailing down to Sam’s still exposed dick, “you wanna?” He licks at his lips encouragingly.

“Do they even still fit?” Sam asks doubtfully and Dean rolls his eyes.

“Yeah!”

He immediately starts stripping off his jeans and boxers and Sam can see his brother his half-hard as he’s stepping into the shorts and pulling them up his legs. When he gets them in place, he holds his arms out in an _I told you so!_ gesture.

“Dude,” Sam says, grinning, “those so do not fit. He can clearly see the firm outline of Dean’s dick through them and the fabric is stretching tight over his brother’s legs, but the smile slowly turns predatory as he thinks of something. "Turn around.”

Dean spins around, lifting his shirt a little higher so Sam can get a clear view of the fabric pinching tight around his ass and there’s no way that can be comfortable, but damn if Dean doesn’t look so fucking good like that.

“Take that shirt off,” Sam says and Dean spins back, grins at Sam and throws his shirt at the foot of the bed, then eagerly climbs onto it and over Sam. Sam reaches around to grab at Dean’s ass, squeezing it through the fabric. Dean bites his lip while he smiles down at his little brother.

“So?” Dean asks quietly, “how do you want me?”

Just to hear that from his big brother’s lips is enticing enough, but he wants to play with Dean first. He grabs Dean’s hips and pulls him until his ass is nice and snug against Sam’s hard dick. Dean starts grinding down onto Sam and Sam lets him, just so he can watch the fabric pull tight over Dean’s dick, a dark spot forming on the shorts where Dean’s leaking through. Sam slides his hand over it, traces the outline of the head and lets his forefinger run over the slit. Dean’s hips jump forward at the overstimulation, but he keeps rocking his hips, breathing coming a little heavier. Sam rubs it again, pressing that wet fabric right against the tip and Dean whines. Sam lets up and instead rubs his palm down the length of Dean’s dick, presses firmly against it so Dean can grind up into his hand and back against his dick.

“Feels good, Sam,” Dean sighs, resting his palms against Sam’s bare chest for more leverage, “need more.” Sam grunts in response and quickly flips them. Dean’s eyes are wide as he stares up at Sam but Sam just smiles back, grabs the back of his brother’s thighs and gets them up in the air, spread wide for him and that fabric stretching so tight over Dean, Sam can see everything.

He slides lower, still holding Dean’s legs open and he presses his open mouth over the head of Dean’s dick through the fabric. He lets his tongue make the fabric even wetter and it’s not an entirely pleasant taste or sensation on his tongue, not like silky smooth skin, but the sounds Dean’s making are enough to keep him doing it. He goes lower, breathing hot air down Dean’s dick until he gets to Dean’s balls where he presses his tongue firmly against them. Dean grabs at Sam’s hair and pulls him closer.

“Need these off,” Dean whines and Sam pulls up to look at him.

“Too tight?” He asks, grinning.

“Not enough, need to feel you…”

Sam groans and, as it turns out, he simply can _not_ resist his brother. He reaches up for the waistband, hooks his fingers in it and tugs the shorts down and off, throwing them aside and watching as Dean’s legs fall wide open.

“ _Fuck_ yeah…” Dean groans and goddamit he looks so beautiful like this. Sam grins down at him and reaches for the lube on the nightstand and, in his over-excitement, spills some over his hand, the bed, and Dean’s thighs. Dean doesn’t seem to mind, or even notice, especially not when he’s split open on two of Sam’s fingers and getting fucked nice and slow.

“God dammit, Sam, just do it already!” Dean throws his head back onto the pillows and Sam does not need telling twice. He pulls his fingers out and rubs whatever’s left of the lube over his dick and then he’s finally sliding inside Dean and it’s tight and hot and so fucking _good_.

“Mmm, _Sammy_ …” Dean whines and pulls Sam down for a messy kiss while Sam pounds his ass into the mattress. Sam knows when Dean’s gonna come because those bow legs wrap high around Sam’s waist and deep groans and moans go high-pitched and breathy and strong fingers tangle in Sam’s hair and Dean’s done for, coming all over his stomach and writhing on Sam’s cock until he’s over sensitive. And fuck, Sam’s pretty sure he’s never seen anything hotter and comes to the sound of his own name being repeated by Dean over and over.

They both collapse on the bed, side-by-side, completely breathless and Sam’s brain can’t function on any levels right now but he manages to get out, “yeah, definitely keep those shorts.”

**Notes for the Chapter:**

> sorry guys. this one seemed to get away from me hah


End file.
